Los Angeles, January 9, 2026 – Jennifer Aniston had an unexpected brush with the past during a recent Hollywood night out, as the Friends star was spotted leaving the Sunset Tower Hotel shortly after her ex-boyfriend John Mayer departed the same hotspot, according to the Daily Mail.
On Thursday night (January 8), Aniston exited the iconic hotel alongside a group of friends, including Molly McNearney, wife of talk show host Jimmy Kimmel. She kept her look effortlessly chic in an all-black ensemble while heading to the valet stand.
Earlier that evening, Mayer, 48, was photographed leaving solo, carrying a book under his arm. He wore a black jacket over a pale blue button-down shirt paired with gray cargo trousers. The timing created a near run-in, reigniting curiosity about their past relationship.
Aniston has since moved on with hypnotist, while Mayer has recently been linked to TikTok personality Kat Stickler.
The former couple dated on and off for roughly a year after meeting at an Oscars party in 2008, ending their relationship permanently in 2009. Mayer later sparked controversy with comments about their age difference, saying in a Playboy interview, “I’ll always be sorry that it didn’t last… But I can’t change the fact that I need to be 32.”
Aniston addressed the split in Vogue, stating, “He had to put that out there that he broke up with me. And especially because it’s me. It’s not just some girl he’s dating.”
Despite past drama, the two have shown signs of goodwill. In 2020, Aniston joined Mayer’s Instagram Live tribute to Bill Withers, reacting with laughing emojis. She added, “We talk, we adore one another. And that’s where it is.”